


His(sex)story 101

by impulse_baker



Series: Introduction to Advanced Kinks (Professor!Verse) [1]
Category: Supernatural
Genre: Age Difference, Alternate Universe - College/University, Bottom Dean, College Student Dean, Come Eating, Dom Castiel, Gratuitous Smut, Light Dom/sub, M/M, Nipple Play, Orgasm Delay/Denial, Porny Pornography of the Pornographic variety, Praise Kink, Professor Castiel, Sub Dean, Teacher Castiel, Top Castiel, using office supplies as...sex toys
Language: English
Status: Completed
Published: 2017-01-24
Updated: 2017-01-24
Packaged: 2018-09-19 15:43:51
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 9,244
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9448514
Author URL: https://archiveofourown.org/users/impulse_baker/pseuds/impulse_baker
Summary: Dr. Castiel Collins is not at all what Dean expected of his history professor. The man is indescribably hot, charming and leaves Dean completely flustered, although he tries to brush it off as a stupid crush.. But what happens when Dean accidentally emails his professor porn with a message that has some very obvious implications?Or...the one where I project my UST about my new amazing professor on Dean and Cas. Because why not?





	1. First Day of the Semester

**Author's Note:**

> HAPPY BIRTHDAY DEAN WINCHESTER!

Dean could hardly believe his luck. He was in his spring semester of his junior year and here he was in a sophomore level history class. It was the only available class he could take to fulfill one of his elective requirements, and there was no way around it. He enjoyed history very much, but he wasn’t excited about having to sit through a class that wasn’t going to teach him anything he didn’t already know. He looked around the room and pretty much all of them looked like underclassmen, with the scarce exception.

The room was in disarray since it was furnished with a number of swivel chairs with attached desks instead of the traditional four-legged chair. There were no clear rows or aisles or columns so he sat down in the middle of the second “row”.

He looked at the time on his phone. It was 1:52 and the professor was standing at the podium at the front of the classroom with his back slightly turned, speaking to who was undoubtedly the teaching assistant. There was a tan trench coat draped across the professor’s chair and Dean internally groaned. This guy was gonna be one of those weirdo hermits who only taught because it was the only way he could conduct research with the university. Fan-freaking-tastic. All his other classes were amazing with great professors, so he assumed it was only fair that he have at least one stupid class and awful teacher.

Dean went back to scrolling through Pinterest, looking for recipes. Finally at 2:00 the professor started handing out the syllabus to the class, so he closed out of the app and locked his phone to put it away. He looked around to receive a handout, but no one around him had passed one to him, so he sighed and made his way to the professor’s podium.

“Excuse me, Professor?” Dean was not prepared for what he saw. His “hermit” professor turned around to address him and Dean thought his lungs collapsed. The man wasn’t the hottest person he’d ever seen and he wasn’t particularly striking, but Dean felt like the floor had disappeared beneath his feet. He could feel his face heat up and he almost forgot how to make words come out of his mouth.

“Yes, what can I do for you?” His smile. His _smile_. And oh god his god damn voice. It was a deep rumble, like brown sugar and gravel being sifted through silk.

“I umm… I didn’t get a syllabus.” He managed.

The professor’s smile widened and his blue eyes twinkled. He swears to god they fucking _twinkled_ like a Disney prince or some shit. “Oh yeah, you don’t get one.” His tone was light and teasing and Dean was hooked. He wanted to hear that voice and that tone for the rest of the semester. No, fuck the rest of the semester, he wanted to hear that voice for the rest of his life. “Here you are.” The professor handed Dean the syllabus and all he could do was dumbly whisper ‘thank you’ and hurry back to his seat. He buried his face in the handout, almost too nervous to look back up at the impossibly attractive man speaking at the front of the classroom. He read the front page.

_Dr. Castiel Collins_

_Office: 609D Tippens Hall_

_Office hours: T, TR 1:00 – 4:00 and by appointment_

_Castiel.collins@spn.edu_

The guy looked a little young to have already earned his PhD, but that just meant he was a genius or something.

“…I did my dissertation on Ottoman Egypt…”

Dean’s ears perked up at this snippet of information. He loved that part of history and the more he listened, the more interested he became in this guy. Apparently they shared the same passions for the same parts of history and if that wasn’t a turn on, he couldn’t say what was. He intently listened to him explain what to expect from the class and all that important stuff and all the while he couldn’t keep his eyes off him. He was probably about six feet tall, had dark mussed hair, a strong shadow of stubble and the bluest fucking eyes he had ever seen. He had kind of a lean swimmer’s build, but he couldn’t really tell too well underneath his black slacks and dark blue button down. What he _could definitely_ tell, was what side the man dressed on, because holy hell, either the guy got off on teaching history (which was strangely doing all sorts of things to Dean’s imagination) or he was just huge even in a flaccid state. Dean licked his lips at the thought.

He was interrupted in undressing the professor with his eyes when said professor was standing near Dean’s desk with his hand outstretched, offering him a stack of notecards. “Don’t want to miss you again.” There was that damn smile again. It was the look of a man who was in on some inside joke he was enjoying way too much and it made Dean’s stomach flip. He tried to smile appreciatively but the heat in his face paralyzed him and he croaked out another weak ‘thank you’ as he accepted the note cards. He took one and then turned to look around to see in which direction to pass the stack, but everyone had already passed enough around, so he awkwardly set the stack at the corner of his desk, careful to not let them fall all over the floor. That would be way too embarrassing. He looked up at the overhead projection on the board and followed the instructions. He wrote his name, his classification, his major, where in the world he had travelled to, and his favorite parts of history. After a few minutes,  Dr. Collins asked everyone to go around and share what they wrote. The first girl introduced herself and then answered the question by saying she enjoyed the cause and effect aspect of history best. One by one, everyone talked about how much they liked learning about the lasting effects of conquests, military influence, repetitive nature of events, and Dean looked at his own notecard and got nervous. They all seemed to understand the question differently than he did. He thought he was being asked to name his favorite eras to study and he felt stupid. He tried to think of something to change his answer to, but before any thoughts could be processed, blue eyes were on him expectantly.

“And your name?”

“Oh uh, Dean. Winchester. I’m Dean. I’m a junior, an engineering major, I haven’t travelled anywhere outside the U.S. because I’m terrified of planes,” the class chuckled and he even heard a few girls around the room ‘aww’ at him, “and my favorite parts of history are the Fatimid and Mughal Empires.”

What he didn’t expect was for Dr. Collins’ face to light up when he was done talking. It wasn’t fair how good the man looked. And it wasn’t fair the effect he was having on him just from talking about the time he spent in Cairo researching for his dissertation. He clearly loved what he did and his obvious enthusiasm was really doing it for Dean. Somehow. This was weird, but he couldn’t tear his eyes away from his very animated professor.

At 2:50, Dr. Collins dismissed them and asked for them to turn in their notecards as attendance for the day. Dean packed up his stuff and stood up, fumbling to untangle his earbuds as he walked to the podium to hand in his notecard. When he looked up, his professor was packing his own things and he smiled in his direction. Dean put the stack of blank notecards next to the pile of used ones and tried to return the smile.

“You know, I use a binder clip to keep my ear buds from getting into a mess like that.” He reached into a pocket of his caramel colored leather book bag and retrieved neatly wound earphones clipped with a binder clip. “Want one?”

“Oh wow. Yeah, thanks, that’s so cool.” His voice sounded so dumb in his own head and he hoped he wasn’t giving himself away. He knew he was an embarrassing shade of red and he could only pray it wasn’t as obvious as it felt. Dr. Collins gave him a clip for the earbuds in his hand and the brief contact between their skin shot sparks through his palm and down his arm, into his core. “Thanks, Dr. Collins.”

“No problem. I look forward to this semester, Dean.”

 _He remembered his name._ He dared one last look at the professor before shuffling out of the room as fast as he could without making himself look like a complete awkward idiot. In all truthfulness, he had no clue why this professor was making him feel so stupid. He mulled it over the whole bus ride home and as soon as he was in his room, he shot a text to his best friend, Charlie, asking to hang out. He didn’t have any homework and he definitely didn’t need to be alone with his thoughts at that moment, and he really wanted to talk to her about this incredible professor.

It didn’t take long for his phone to notify him that she had text back.

_Queen Charlie Bradbury: Yeah come over biiittcchhhhh_

_Dean Winchester: Sweet. On my way_

Luckily, and kind of by design, Charlie lived in the same apartment complex as Dean so it was a short walk to her doorstep. He rang the doorbell and Charlie swung the door open.

“Hey! How was class?”

“Oh my god, you’re not going to fucking believe it, man.”

“Did you sprout a third nipple?”

Dean huffed at her. “Shut up, dude this is serious stuff! It’s one of my professors.”

“Your professor flashed the class their multitude of nipples? How many nipples were there?”

“Stop saying the word nipple.”

Charlie just laughed and waited for him to continue.

“Ok, so you know that stupid history class I have to take? Well the professor is like… I don’t even know, man. He’s _smoking_. Like hottest guy ever. But not in a physical way. He’s hot and whatever, but not like Dr. Sexy hot, he’s like… Benedict Cumberbatch hot.”

She cocked her eyebrow at him. “Oh Dean, I’ve heard this before. Remember last semester’s calculus class?”

“No no for real this time. This guy is like a different kind of hot, it’s so weird. He’s like… He’s got this unbelievable smile and –”

“Dean, Steve Buscemi could smile at you real nice and you’d swear the man was Chris Hemsworth.”

“No, this wasn’t just looking at him though! It was everything. The way he talked, and like how passionate he was and I swear I lost brain function the whole time. I could barely talk and my face kept getting hot and honestly I have no clue what it was, but he’s just… He’s _wow_. Ten out of ten, would bang. And look,” he pulled out his clipped, untangled earbuds, “he showed me how to keep these tangle free! The man is a genius!”

“Oh my god, you got all flustered over your professor? I have got to see this guy. You think he has a sister that could do whatever he’s doing to you, to me?” She joked, and Dean tried to scowl at her through the laughing.

“Oh but the biggest thing, and I mean that literally, was this guy’s dick.” Charlie briefly looked shocked and Dean could imagine all the things that sentence could have sparked in her active imagination. “No like I could see the outline through his pants. This man is _packing_. And I’m pretty sure he wasn’t hard or anything, just normal.”

“Orrrrrr maybe he _was_ hard! Maybe, you were doing it for him, too!” She was practically squealing at this point. Dean wouldn’t believe it, but the hardening between his legs certainly seemed to be having fun believing it.

“No there’s no way. He’s a doctor, so he’s got to be older and he’s probably married and whatever. And plus, he’s a professor. We can’t… you know. Have _relations_ with that man.”

“Okayyyy Bill Clinton!” Charlie held her stomach as she laughed and tried to catch her breath.

“I hate you.”

“No you love me.”

 

That night Dean reread all the syllabi he received that day and marked his calendar with due dates and such. He noticed what he was sure had to be a mistake on Dr. Collins’ syllabus and composed a quick email to ask him to clarify, and then tried to turn in for the night. As Dean was getting ready for bed, he couldn’t get a certain pair of blue eyes out of his head. He took a quick shower, brushed his teeth and put on a pair of boxers to sleep in. He looked down at his relentlessly enthusiastic dick that was making shy attempts at getting interested. This wasn’t going to go away, so he opened his laptop back up and scrolled through the porn website until he found what he wanted. He settled into his bed and pulled the covers just over his bent knees and slid his boxers down to around his ankles. The laptop was situated in perfect view, Kleenex were within reach, and his earbuds were in, so he pressed play.

On screen a guy in a tight school uniform was sneaking behind a large desk, shuffling through drawers until he found whatever paper he was looking for. He read it over and smiled when suddenly another man entered the room. He was wearing a cheap black suit, blue tie, with thick framed glasses. The student was chastised for trying to steal the exam answer key and promised him a punishment to teach him a lesson. Dean rolled his eyes at the cliché but the two actors were really hot, so he kept up his loose strokes.

The door was locked and the student was ordered to stand at the blackboard and write some ridiculous line over and over again. The teacher pulled the student’s pants down to reveal his perky ass – of course he wasn’t wearing underwear – and he gasped. The teacher started eating his ass vigorously but ordered the student to keep writing until he was told to stop. Both men on screen were moaning now, deep and throaty and _now_ they were getting somewhere. Dean’s strokes stayed slow but his grip had tightened slightly. The student was bobbing his ass down to spear himself on the teacher’s tongue and it wasn’t until he had written three quarters of the way down the board that the teacher stepped away. He instructed the student to strip and bend over his desk so that he was in nothing but his knee high socks and shoes, pushing his ass in the air. The camera got a good shot of the man’s sloppy loose asshole and Dean swallowed, his breath getting labored. The teacher delivered five swift, hard slaps to his ass with one hand while his free hand undid his pants. He pushed his thumb into the waiting hold in front of him but didn’t prep the student much beyond that before pushing his dick inside. Dean felt a brief moment of sympathy for the student because he knew it wasn’t fun or sexy to get a cock up the ass with minimal prep. That thought was pushed out quickly when the student was practically screaming out happily a chain of ‘ _oh yes sir’_ and _‘yes please’_ and other profanities. In return, the professor was growling at the writhing man beneath him that he would teach him a lesson and that he was the teacher the student needed to teach him what he needed and how bad of a student he was. Dean was panting hard at this point, beads of sweat at his hairline as he pumped himself through the scene unfolding on his laptop screen. He was getting really close, but he wanted to hold out until the student came, which based on the noises and faces he was making, wouldn’t be much longer. The teacher pulled out and came all over the student’s ignored erection, then, using his spend as lube, he roughly stroked the student’s cock until he shot cum all over the teacher’s hand. At the same time Dean jerked through his orgasm and closed his eyes, seeing blue eyes and dark hair behind his lids as he felt the warm sticky liquid cover his hand. He let out a breath and looked at the screen. The camera was showing a close up of the cum that was sliding down the student’s dick and over his red gaping hole. That was fucking hot and a pretty good orgasm. He cleaned himself up and threw the Kleenex away before returning to his laptop. He copied the link into an email to send to Charlie. She couldn’t really get off to porn that had an absence of women, but she always appreciated watching a well shot porno, regardless of the represented genders. In the recipient box he typed a C and selected the first one that came up in his contacts since Charlie was always the first C in his list. He quickly typed in the message box _‘Guess who I thought about when I watched this ;) ‘_ ,hit send, and closed his laptop, and blissed out, fell into a deep sleep.


	2. Mistakes Were Made...

He met Charlie for lunch the next day and he couldn’t wait to hear what she had to say about the video he sent. She was something of an expert porn analysist. Which, now that he thought about it, was kind of fucking weird.

She joined him with her salad in hand and promptly began eating. He looked at her expectantly, waiting for her to say something.

“What?”

“You know what!”

“Winchester, I can’t read your mind.”

“What did you think of the video?”

“What video?”

Dean paled. Charlie checked her email every other hour, on the hour. She should have seen it. He had pressed ‘send’ for sure, and he hadn’t gotten any emails that his message bounced or failed to send or anything. That could only mean…

He frantically checked his ‘Sent Mail’ folder in his email and the world collapsed around him. The most recent message, sent last night was addressed to castiel.collins@spn.edu.

“Fuck.”

“What?”

Dean put his head down on the table and wanted to curl up and die. This was hands down the worst thing that could have ever happened to anyone in the history of everything.

“Dean, what happened?”

He just pushed his phone to her face so she could see for herself. Instead of the sympathy and comfort that she was obliged to provide as his best friend, Charlie burst into a fit of uncontrolled, tearful, loud laughter.

“OH MY GOD this is the best thing that has ever happened in the history of ever!” She howled.

“What the fuck do I do?” He wailed. That was it. He couldn’t go back to class. He would have to transfer schools. He would have to leave the country, change his name, erase any trace of his existence, adopt a new identity.

“Nothing. You do nothing because you’ve already done EVERYTHING!” She was still laughing but she had her hands on Dean’s arm in a gesture of solidarity.

“Charlieeeeeee what the fuck do I do?”

“Ok. You go to class. Like normal. You act completely normal. Don’t say anything unless he says anything. And if he says anything, tell him you’ll do _anything_ for him not to tell anyone.” The she-devil winked at him and dissolved into another fit of hysterics.

“I hate you. I hate porn. I hate technology. I hate myself. I hate everything.”

“Don’t worry. Best case scenario he accepts your offer and you get to blow him in return for pretending it never happened.”

“Fuck you. Worst case?”

“You get reported for sexual harassment. But don’t worry, I can make that go away. That’s the beauty of the internet!”

“No. Fuck the internet.”

“It’s ok, Dean. You’ll be fine. Now come on, let’s get some pie to cheer you up. They have apple on special today!”

 

Since he had history on Mondays, Wednesdays, and Fridays, he spent all of Tuesday dreading Wednesday, and when the day rolled around, he dreaded going to class. It was the last one of the day and he considered just skipping and going home. But attendance was mandatory, and he really didn’t want to fail, but he also didn’t think he could face a professor he sent porn to. He didn’t know what to do, so he just ended up going to class. When Dr. Collins entered the room Dean drew his breath in sharply. He was dressed in a very well fitting black suit that let everyone see what an absolutely athletic ass he had. Not only that, but he was wearing a blue tie and _thick framed glasses_.

This had to be a coincident. There was no way he was wearing the exact teacher outfit from the video on purpose. It was impossible. Whatever the reason, he looked extremely hot. Undeniable sex on legs. Dean wasn’t the only person to notice. The three girls in front of him were trying to subtly take his picture. He watched them snapchat multiple pictures of the professor and he tried to pay attention to something else but there was nothing in the world more interesting than the suit clad man at the podium currently looking over his glasses at his laptop screen. Dr. Collins looked up momentarily and their eyes met and sure enough, Dean’s face flushed. He wanted to avert his gaze but he just couldn’t. He was held there in the clear waters of blue staring back at him.

“Dean, I just wanted to let you know I received your email.”

 _Oh what the fucking hell?_ Was he about to say something in front of the whole class? That was too fucking far, he wasn’t going to let that happen.

“And I want to thank you. I did, in fact, make that mistake with the due dates, so if you all could, please correct the first essay due date from February 5th to the 6th. Thank you for that, Dean.” His smile was genuine, but the teasing glint was still there. Dean unclenched his fists and relief washed over him. He had completely forgotten about the first email, and he sat back in his chair, more relaxed now.

He had no trouble concentrating when class started. Dr. Collins was lecturing about pre-Columbian Mesoamerica, and despite already knowing the information, it was still infinitely interesting. Even with his distracting wardrobe Dean’s concentration was tuned in on everything he was saying. As he moved around the front of the room Dean’s eyes followed him. He watched the movements of his hands as they gestured for emphasis, and they were the most sensual hands he had ever seen, even from the distance, and he noted an absence of any rings, so he probably wasn’t married. They looked strong and their movements were fluid and exact. He watched his tongue dart out to moisten his pink lips every time he stopped talking. He watched his shirt pull over his muscles every time he turned to write a term on the blackboard. His eyes fell below the belt where the same bulge was visible behind the fabric. He could’ve easily been mistaken, but it seemed slightly more noticeable than last time, but that could be because of the fit of the pants. Possibly.

Dean actively participated in class, loving the way the professor praised his active insight, the way he would smile at him rewardingly. Not only was he eye candy, but Dr. Collins really knew his stuff and gave really great responses to every comment made in class. Smart really is sexy.

At the end of the lecture, Dean was packing up when Dr. Collins’ voice stopped him.

“Did everybody get a chance to sign the attendance sheet that was passed around?”

How did he get skipped again? He swore his classmates must have hated him or something to have not passed him the attendance sheet. He timidly raised his hand and Dr. Collins smiled at him.

“Please sign in so that you get credit for being here, Dean.”

He was in the middle of writing Winchester, when that rich voice interrupted him.

“I’d like to discuss that email you sent me further, but unfortunately I have a meeting to get to right now. Would you mind stopping by my office after class on Friday?”

He swore all the organs in his body sank into some black hole that formed in his core. All the breathlessness, the blushing, the shy glances, were all so unusual for Dean. He was a confident man, not this blundering mess he was showing Dr. Collins. So, with all strength he could muster, he held eye contact and replied in the affirmative.

“Wonderful. I’ll see you on Friday. Enjoy the rest of your day, Dean.”

He had no clue what to expect, but if today’s outfit was a sneak preview, he couldn’t wait.


	3. The Gift of Orgasm

Friday morning Dean woke up earlier than his alarm and really pampered himself in the shower, taking time with his lathering and scrubbing, enjoying the steam and smell of his body wash. He was nervous as hell, because Dr. Collins may have not been alluding to what Dean thought. He could be wanting to tell him how creeped out he was and how he wanted Dean to switch to a different class. But Dean wanted to ride this high for as long as he could. If in the moment of truth he was disappointed, that would be ok. He would deal with it at that time. For now, he would relish in the excitement. Plus, it was his birthday. He was going to make the best of it.

History class couldn’t come soon enough. And then when it came, it couldn’t end fast enough. As soon as class was dismissed – he made sure he signed the attendance and gave Dr. Collins a smile before he left – he was making his way to the sixth floor to find the professor’s office. If it was bad news, he wanted to get it over with. If it was good news, he wanted to get started as soon as possible. He stopped at the bathroom on the way there to wash his face and his hands to calm his racing nerves.

He finally found the office. It couldn’t have been in a better place. It was in the very back corner of the sixth floor and the walls were clearly _very_ thick. God must really love him because his birthday was looking better and better. He knocked and tentatively pushed the door open. Dr. Collins was sitting at his desk, reading some book. When he heard Dean, he looked up and smiled, that same open, bright smile.

“Please, sit down Dean.”

His tone was still light, not at all what Dean was expecting, but he was willing to see where this went.

“First of all, I want to thank you for pointing out the mistake in the syllabus. That could have led to a lot of confusion.”

“Oh. Yeah. No problem. I mean, it helps me as much as it does anyone else, so yeah.”

“You have quite the eye for detail, it seems?” Both of their eyes flickered up and down each other briefly, and Dean knew what he meant.

“Yeah I uhh… I notice all kinds of things.”

“Hmm. That brings me to the other matter at hand. The _other_ email.”

Here it was. This was the moment of truth. Dean involuntarily held his breath.

“I must say, I was taken rather by surprise. I was very curious as to what my student felt was necessary for me to see, so as to send a link at that hour. And when I opened it, you can only imagine what I must have been feeling then.”

His voice was gradually getting deeper, more gravelly, and Dean’s jeans were feeling a little more snug than they were moments ago.

“Would you venture a guess as to what happened when I watched the video you sent me, Dean?”

Dean’s throat had gone dry and even if it hadn’t, he didn’t think he could form coherent sentences, so he shook his head.

“I went back and read the message that accompanied the link and I was so tempted to reply to you. I wanted to seek out confirmation of what I didn’t dare hope was the meaning behind the email. I wanted you there, Dean. I wanted you to tell me exactly what you were thinking when you sent it to me. I wanted to know what exactly your intentions were. I wanted to know if you enjoyed the video as much as I did.” His tone had dropped at least an octave and Dean wanted so desperately to give him the answers he wanted, he wanted to do whatever Dr. Collins wanted him to.

“Dean. Tell me, now. Tell me who you were thinking of. Tell me what you were thinking.”

“Dr. Collins – I…”

“You may call me Castiel, Dean.”

“Castiel.” He experimented with his first name. It was nice. It was weird. But it fit.

“Yes, go on.”

“I was…I was thinking about you, Castiel.”

“And?”

“I wanted you to… I was thinking about what it would be like. For you. I mean… for us. To be like that.”

“Like what, Dean?”

“Like the guys in the video.”

“You want that?”

Dean nodded, eyes wide.

“I need to hear you say it, Dean. I need you to verbally communicate to me if that is what you want.”

“Yes, I want to do what they did.”

“With who?”

“With you.” He barely managed to whisper. He had never gotten so worked up like this with just a conversation. Not even dirty talk during sex got him worked up to this extent.

“Louder, please.”

“With you, Castiel.”

He momentarily wondered if he did something wrong because Dr. Col – _Castiel_ – got up and went to the door. But instead of leaving, he locked the door and returned to stand over Dean.

“I must tell you, for your peace of mind, the entire floor is empty. Everyone who has an office up here is gone for the day, seeing as it is Friday. On top of that, these walls are very thick, designed to contain sounds within the rooms. Do you feel comfortable.”

Dean nodded.

“Dean, I need to verbalize your every answer to me.”

“Yes.”

“Good.” He brushed his fingers over Dean’s jaw, making him shiver. He ran his other hand through Dean’s hair several times and Dean eased into the feelings of his hands on him, leaning into the fingers grazing his cheek. “Do you have a safe word?”

This caught Dean off guard. What the hell did he need a safe word for? His panic must have been apparent to Castiel because he bent to eye level with Dean and put his palms on either side of his face.

“I want to do what they did in the video, but better. Does that make sense? I want to make you feel good. I won’t do anything to cause you any real pain, and I won’t do anything without your consent. But if it gets to be too much, I need you to have a word to let me know that I need to stop. I don’t want to hurt you.”

Dean chewed the inside of his cheek. This was exciting, but he’s never gotten into anything that he needed a _safe word_ for. The sincerity in Castiel’s eyes comforted him though. This man wouldn’t hurt him. He wanted this, and if this is how he wanted to do it, then he would try it.

“Impala. That’s my word.”

“That’s perfect. Can you repeat it for me?”

“Impala. You’ll stop if I say it?”

“Yes, as soon as you say it, I’ll stop everything.”

That was reassuring. He could do this. It was actually really exciting.

“I’m going to start now. Are you ready, Dean?”

“Yes.”

“Oh and Dean, are you clean?”

“Yes.” As soon as the words were out of his mouth, there was a visible shift in Castiel’s countenance.

“Hello, Dean. Thank you for coming to my office. We have quite the issue to discuss.”

He was confused for a moment. Did he have amnesia or some shit? But then it all clicked. They were _in a scene_. This just got that much more fucking exciting. He could definitely play along with this.

“What did you need to see me about Castiel?”

The sharp raise of his eyebrow and questioning look kind of took him aback. What did he do wrong already?

“You will refer to me as Dr. Collins, or _sir_ , seeing as I am your professor, Dean.”

 _Ohhh fuck yes._ He could get on board with this train.

“Sorry, sir, I apologize.”

Castiel narrowed his eyes and then settle back in his chair. “As I was saying, we have quite an important matter to discuss, which coincidentally has to do with your utterly clear lack of respect. Do you know what I am referring to, Dean?”

He shook his head.

“ _Dean._ I asked you a question using my words. You will answer me in kind, using words.”

“No sir, I don’t know what you’re referring to.”

“Your email, the one you sent criticizing the syllabus I put together. I don’t appreciate you trying to correct me, as if you know better. Is that what you believe? That you know better than I?”

“No sir, of course not, sir.” This was turning Dean on a lot more than he could have thought possible.

“You seem to have a streak of disrespect and I’ve come to the conclusion that you must be reprimanded if your behavior is to change. Would you agree?”

He was getting nervous at the direction this was going in. _Reprimand?_ As in… punish? He had watched some BDSM porn before and that shit was kind of fucking scary, not his thing at all. He considered safe wording out and dropping the whole thing, but he decided against that. He would stop this if it actually became too much, but not until then.

“Yes, sir, I agree.”

“Good. Now, stand up, remove your clothes, and fold them neatly on the chair you are sitting in.”

He followed directions and his insatiable and ever interested dick was pretty much almost completely hard now, standing proudly under Castiel’s eyes.

“Good. Now bend over my desk and bring your hands together, crossed at the wrist, behind your back.”

He pressed his heated face against the cool surface of the desk, which he noted smelled like disinfectant. If Castiel did that for him, knowing he’d be rubbing his face all over it, that was really fucking considerate. He crossed his hands as instructed and then felt some kind of silky material wrap around his wrists. It was tight enough that he wouldn’t be able to break free, but not too tight that it was uncomfortable. Castiel smoothed his hands over Dean’s body and bent over him, pressing his chest to his back.

“Are you alright?” He whispered, deep and barely audible.

“Yes, sir.”

“Perfect.” He pressed his lips softly to the nape of Dean’s neck. “So perfect.” He whispered one more time before resuming his upright position behind Dean. The contrast between the position he was in and the warm fluttery feeling in his stomach from Castiel’s praise was amazing, better than what he could have ever imagined. He could do this.

Large, warm hands were still rubbing circles over his back, his hips, the taut globes of his ass and the backs of his thighs and it felt good. This didn’t really feel like a punishment, if he was honest.

“Now, I’m going to spank you, Dean. But while I am doing so, I am going to name an empire and I want you to respond with a significant word or concept that is related to said empire. For every second after three seconds that you wait to answer, you get an additional spanking. Do you understand?”

“Yes, sir.” Dean could do this. He loved history. Piece of cake. And then he saw Castiel take out a medium sized, glossy, paperback book. And he recognized it as their primary text for the class. Could he really not just name a bunch of empires off the top of his head?

 _WHACK_. “Qin Dynasty.”

OH FUCK. The bastard was using the damn book to smack his ass, and it kind of really tingled!

“Dean, don’t forget your time limit. This is the first one, so I will repeat myself and hold back on the additions if you can answer in a timely manner. Qin Dynasty.”

Dean’s mind was a little shook from the shock of what was actually happening, but he regained enough brain function to think quickly. He could do this. “Great Wall of China.”

“Excellent.” _WHACK_. “Mongolian Empire.”

“Silk Road.”

“Very good.” _WHACK_. “Portuguese Kingdom.”

His eyes were starting to water a little, but he had to think on his feet. “Treaty of Tordesillas.”

“Wonderful.” _WHACK_. “Ottoman Empire.”

“Janissaries.”

The praise, followed by a sharp smack, followed by an empire continued one after the other, and it was getting harder for Dean to ignore the stinging of his ass and thighs and think of a significant thing related to whatever word he was given. But he could do it. He briefly thought of safewording out but muscled through. He lost count of the slaps but finally after an easy answer of East India Trading Company for British Empire, the smacks stopped.

“You did so beautifully, Dean. So well. I’m so proud. So impressed.” Castiel whispered into Dean’s ear, placing soft kisses along the outer shell, at the soft skin behind the lobe. He was using the book to smooth over the stinging skin of Dean’s rear end and he had to admit, it kind of felt good. His cock which was hanging off the table was leaking steady pearls of precum and it was aching from being ignored and so turned on at the same time. There was nothing to give him any sort of friction and he was becoming very aware of his need for release.

He heard the book get tossed onto some unseen surface and then felt the hot, moist, flat of Castiel’s tongue lave over his sore ass. His hips bucked at the sensation but Castiel’s strong hands steadied him and continued his work. He sucked and licked all over his ass and where his ass and thighs met and he got torturously close to his perineum but never actually giving the sensitive spot any attention.

Dean was moaning and whimpering, trying to push back against Castiel’s tongue, but his firm grip wouldn’t let him budge. There was heat and pain and excitement and comfort all pricking around Dean’s ass and he wanted more. Not just of the excitement of the situation and comfort of his tongue, but he wanted the heat and the pain, too. He wanted everything and anything Castiel would give him.

“I’m going to untie you now and I want you turn around and lay on top of the desk, on your back, and then raise your arms back over your head.”

He hurriedly obeyed, appreciating the cold surface of the desk against his ass. He watched Castiel, who was still fully clothed, rebind his hands above his head with his tie.

“Bend your knees and plant your feet flat on the desk. I’m not going to tie them down, unless you can’t stay perfectly still. Can you do that for me?”

Eager to please, Dean nodded his head, then quickly said “Yes, sir.” It was a breathless whisper, but it was enough.

In this position, he was completely exposed, legs apart, arms above his head, vulnerable. Cas walked around him, keeping his eyes fixed on him. The room felt almost unbearably quiet while Castiel took in the sight of Dean, presented fully in front of him. Dean felt very cold after having Cas so close during the spankings. He felt like he couldn’t feel anything, like there was nothing even to feel. He could acknowledge the hard surface of the desk beneath him but it didn’t _feel_ like anything. He was getting anxious and almost started squirming, but he remembered Castiel’s request to stay perfectly still. He could do this. So far everything Castiel had done had felt incredible, and he trust him to continue that. So he would just have to do what he said and trust that he was in good hands.

It finally paid off when Castiel’s hands finally made contact with his chest. He rubbed over the soft part of his stomach, traced his fingers over his nipples and then flicked. Dean gasped. That felt _good_. Any sensation now was welcome but the attention he was getting now was delicious. One at a time, Castiel would alternate between rubbing circles with his index finger, pinching, and flicking his nipples, until the nubs were hardened and red. Dean wasn’t prepared for the sudden hot suction against his chest and he gasped for air. His tongue flicked and circled and his teeth nipped only for his tongue to soothe again, and Castiel worked so quickly, so attentively that Dean wasn’t sure where the pain from the teeth ended and where the pleasure from the sucking started. It was euphoric, this sudden onslaught of concentrated sensation after the long void.

“Oh fuck, yes! God, _yes!_ Fuck, sir! Mhhmhmhmm that’s so good, feels so good, sir. Aaauuhhh, sir!”

Castiel groaned in approval at the sounds he was making and continued his ministrations. He went on tirelessly for what could have been minutes or hours, but Dean was lost in the sensation. His cock was throbbing now, and it hadn’t even been touched.

“Mmmhhmm sir, you feel so good, so fucking good! I’m so hard, it hurts, sir. Ughhaahh!” He yelped when Castiel used his teeth to suck one of the pebbled nubs in particularly hard and he looked down at him. His blue eyes were on his cock now, as if he had forgotten about it while playing with Dean’s nipples. He swiped his thumb to gather the small trail of precum that was leaking from the head and then brought it to his mouth and licked it clean. Dean’s cock jumped at the sight and without thinking, bucked his hips. That was a mistake. Blue eyes flashed back up at Dean and then he moved so that he was standing in between Dean’s legs.

“Dean. I told you to stay completely still.”

“I’m sorry sir. But I couldn’t help it, sir. I’m so sorry.”

 _WHACK_.

“What was that for?!”

 _WHACK_. “That was for addressing me without the proper respect. The first one was for lying.”

“What did I say wrong, sir?”

“You can _always_ help it, Dean. A person is never not in control of their actions. It doesn’t matter what the situation is. You can always help it. I don’t want you to use that excuse ever again.”

“Yes, sir…”

“What’s that?”

“Yes. Sir.”

“I don’t appreciate the tone of voice.”

Dean thought he was just being ridiculous now. It was an accident, he was just so turned on, he couldn’t control that his hips just moved in response. But Castiel wasn’t having any of it. He dipped his head down and licked the head of Dean’s erection, but Dean kept himself still, until Castiel swallowed the entire length in one swift motion. It was too much, too overwhelming for him to stay still and as soon as his hips left the table, Castiel was off of him, standing at a distance with his arms crossed.

“Do not give me that look, Dean. Listen to me. You couldn’t help it, is not an excuse, not a reason, not a valid statement. You will learn that today, Dean. That’s important to me that you learn that. People are always in control of their own actions.” He stepped around to a cabinet and opened it, pulling something out and keeping it in his hands so Dean couldn’t see. He returned to the desk and emptied his hand. Dean looked down and saw about ten binder clips. What the fuck was he going to do?

“Sit up, with your hands in your lap. I’m going to clip these to your nipples. For every time that you refuse to restrain yourself, I’m going to add another. Understand?” Dean’s eyes widened. He didn’t know if he was going to be able to do this. Everything else was fine, but this was… Different. But, that didn’t mean bad. He always had his safe word.

“Yes.”

Castiel pinched the skin around Dean’s nipples and clipped a binder clip around the hardened nub. It didn’t hurt as bad as he thought it would, but it wasn’t as good as his mouth had been earlier. Then Cas knelt between his legs again and grazed his fingers along the shaft. Dean breathed in. He could do this.

“Oh. And Dean? You absolutely may not cum until I allow it.”

“Yes, sir.”

Castiel fisted Dean suddenly and gave it two firm tugs in _just_ the right way, and oh god it was amazing. His hips twitched, but he kept them down. The rewarding smile he earned from Castiel was worth it. He removed his hand and pushed his tongue against the slit and flicked his tongue at it rapidly. It was getting harder and Castiel didn’t seem to be intending to stop any time soon and Dean’s hips thrust forward, seeking out more. It was just so good! How could he be blamed?

Castiel looked him in the eye, almost sadly, and attached another clip to the end of each one that was already pinched around his nipples. The extra weight stung and Dean bit his lip. This… this wasn’t such a good feeling.

“Dean, listen to me. You. Are. Always. In. Control. It doesn’t matter how good it feels. You are the master of your actions. You are not supposed to move, therefore, you will not move. Understand? If you can hold yourself back through five consecutive motions, I will remove the clips. If not, I will continue to add them.”

“Yes, sir.” He was starting to make more sense. He didn’t know if that was the desire to get the damn clips off that was dictating his resolve, or the thirst to see Castiel smile again, but whatever it was, it set his determination in stone. He would do this. He would control himself. He would listen to Castiel. With each test, he removed an article of clothing, starting with his shirt, then his belt, then his pants, then his shoes, then his socks.

Only one more clip was added until Dean could sit through Castiel’s condition. As soon as he removed Dean’s weeping cock from his throat, he smiled and detached the clips and kissed at the nubs tenderly.

“So good, you did so well, Dean. I’m so proud. You’re doing so well.” The smile back, the one that left Dean speechless, blushing, and _wanting_.

Finally, _finally_ those lips were on his lips and they were kissing. It was gentle but demanding, and they moved together, a dance of tongues and lips and teeth. Castiel licked the roof of his mouth, making him moan into the kiss. He could spend the rest of his life like this, just kissing him, just sucking his plump bottom lip, just feeling his tongue against his own.

They broke the kiss and Castiel pressed their foreheads together, both breathless. “So beautiful. So brilliant. I’m so proud, Dean. You’re doing so well, so beautifully.” Dean keened at the words and timidly nuzzled his nose against the side of Castiel’s face. This felt so good, so impossibly good and he had no idea how.

“Lay down, Dean.” He kissed his way down his body, paying attention to all the abused spots, pressing adoring kisses and soft licks to them, drawing out quiet moans from Dean. Before he could register what was happening, Castiel’s tongue was pushing past Dean’s puckered hole. Spit dripped down his ass and Castiel rubbed his thumbs over the slick perineum, making Dean gasp and writhe above him. Where his actions were first gentle and slow, they were now relentless and hard and fast. His other fingers were crooking around the rim of his hole and it was almost too much. Dean didn’t think he was really a loud partner in bed but Castiel was reaching inside him and pulling out all sorts of noises he didn’t think he could make.

He heard the click of a cap and the tearing of foil, but couldn’t see what was happening and he assumed it was lube, getting excited with anticipation of what was to come. Instead of lifting up to align himself, Castiel continued to work his tongue in and out but the blunt cold tip of something hard joined in. Then it replaced his tongue completely and _holy fuck_ what was that? He could tell it was wrapped in a condom, but it was hard and angular and kind of wide.

Whatever it was, it hit his prostate full on with a flat head and Dean fought every fiber in his being not to arch his back. He could hear hinges squeaking as Castiel moved it in and out, and his mind raced between the onslaught of attention his hole and prostate were getting and trying to figure out what the fuck Castiel had pushed inside him.

He was getting so close, he could feel all the tell tale signs that he was about to cum and he tried to suppress it, to push it back down.

“Please, sir, please! Augghhh god ohhhhhh fuck, I’m going to cum. Please, I’m going to cum!”

“Hold on, Dean. Just a bit longer, hold off until I’m inside you. I want you to cum on my cock. Not this stapler. I want my cock to push out every drop of cum you have. I want your ass to milk my cock and squeeze around it while we cum together. Don’t you want that, Dean? Don’t you want my cock inside you before you cum?”

“Unghhh, ohhh yes, that’s what I want, sir. That’s what I want. Please, please, please!” Dean had never begged before and here was his history professor, a man with a PhD in history, making him beg to cum on his cock, and – WAIT. _STAPLER?!_ He had a stapler fucking into his ass. Holy hell, that shouldn’t be as hot as it was, but the wrongness of it, the strange excitement that came of using something so mundane to bring him this much pleasure was enough to make him forget any reservations he could possibly have about having a stapler in a condom, shoved up his ass.

At long last, Castiel stopped and slicked himself up, raised Dean’s legs so they were draped over Castiel’s shoulders, and then pushed in, bottoming out all at once. Dean wasn’t wrong about Castiel being big. That didn’t quite do him justice. He was easily well above average, in length and in girth and he felt so wonderfully full. He could feel every inch of Castiel’s velvety hot skin pushed against his walls, and when he started moving, Dean saw stars. He needed to cum so badly, he had suppressed multiple orgasms already and he could feel his aching need coiled low in his gut, waiting to be released.

“Auhhh! Unhghhh, Dr. Collins! Ahhhhhh, sir! Mmhmmhmm sir, ohhoohhhh god, yes, that’s so fucking – auuuhhhh _CASTIEL_!”

“That’s it, Dean, just a little bit more, hold on, just… aughnghh! A little bit more!”

Castiel thrust into him and held onto his legs the whole time, holding his gaze. He wouldn’t be able to hold off much more with the way Castiel was moving. He needed to cum. Castiel kissed his inner calf that was clenched by the side of his head and then he bit down gently on the other calf, groaning, panting, as if close. Dean hoped to god he was close because he needed to cum.

“Alright Dean, let go, cum for me, let me see your cock cum.” The orgasm that followed was the kind that had his thighs spasming, his knees trembling, and his ass clenched. It was a toe curling orgasm, the kind that rushed through him arching his back and screaming out Castiel’s name. At the same time, he pulled out and jerked himself onto Dean, shooting his seed all over Dean’s overly sensitive dick and dripping fast over his used hole. If he hadn’t just had an earth shattering orgasm, Dean might have gotten hard again when Castiel leaned down to lick up their combined cum off Dean’s ass. He swallowed thickly and then without warning swallowed down Dean’s cum covered cock, eliciting another scream and a violent shudder to pulse through his whole body.

“ _FUCK! OAAUUHH CASTI – AHH CAS!”_

He released his twitching, soft member out of his mouth and swallowed another mouthful of their combined seed. Dean’s whole body was an over sensitive bundle of nerves covered in sweat, and utterly blissed out. He had never in his entire life had an orgasm that amazing. Castiel leaned over and gathered Dean to his chest, bringing their lips together and Dean could taste himself and the professor on his tongue. In one swift motion, Dean was being lifted up, cradled, and then laid down on the couch in the office and Castiel was settled snugly behind him with his arms wrapped around his midsection.

“Wow.”

Castiel chuckled softly. “I agree.”

“That was… wow.”

“You were incredible Dean. Absolutely amazing. I’ve never seen anything so beautiful.”

“Come on, you’ve seen the Al-Hambra Palace.”

“Dean, I assure you, the palace pales in comparison to you, especially the way I got to see you today.”

“Whatever you say, Castiel.”

“You could call me Cas, if you want.” He said this part rather quietly, almost as if he were unsure.

“I’d like that. Castiel is nice, but kind of a mouthful. Cas.”

“I like it, too.”

Just then Dean’s phone buzzed. He was too comfortable to get up so Cas got his phone for him out of his backpack. It was a text from Charlie. He opened it when Cas was settled closely behind him.

_Charlie Bradbury: Happy Birthday biotchhhh (again)! I love you! See you at dinner!_

He could feel Castiel quirk his eyebrow behind him.

“I wasn’t aware it was your birthday. I apologize if I kept you from any plans. I would’ve gotten you something, had I known.”

Dean laughed. “Trust me, there was nothing I would’ve rather been doing. And consider that the best birthday present ever.”

“I didn’t give you a present, Dean.”

“Of course you did! You gave me the gift of orgasm!”

**Notes for the Chapter:**

> I sincerely hope you enjoyed or at least had fun through this smutty mess. Thank you for being an outlet for the chaos that is my brain. I love you all!
> 
> Come say hi on Tumblr! http://compulsive-baker.tumblr.com/


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